Azabicyclo[3.1.0] hexane derivatives have been extensively known in the prior art for the treatment of central nervous system disorders, as antimicrobial agents, as having anxiolytic and analgesic activity, as vanilloid receptor ligands and for the treatment of Hepatitis C virus infection. Depending upon the selection of different types of substituents on the main scaffold “3-azabicyclo[3.1.0]hexane”, the specificity or affinity for the different targets varies.
For example, U.S. Pat. No. 4,435,419 (American Cyanamid Company) discloses 3-azabicyclo[3.1.0]hexanes exhibiting antidepressant properties. U.S. Pat. No. 4,131,611 (American Cyanamid Company) discloses 3-azabicyclo[3.1.0]hexanes having anxiolytic and analgesic activity.
PCT application WO 2002066427 (DOV pharmaceuticals, Inc.) discloses (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane. PCT application WO 2003017927 (DOV pharmaceuticals, Inc.) discloses (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane. DOV's PCT applications WO 2008153937, WO 2007016155 and WO 2006096810 further disclose substituted 3-azabicyclo[3.2.1]hexanes. PCT application WO 2008057575 (DOV pharmaceuticals, Inc.) discloses arylbicyclo[3.1.0]hexylamines.
Glaxo's following PCT applications disclose 3-azabicyclo[3.1.0]hexane derivatives: WO 2009027293, WO 2008074716, WO 2007113258, WO 2007113232, WO 2007022935, WO 2007022934, WO 2007022936, WO 2007022933, WO 2007136223, WO 2006133945, WO 2006108701, WO 2006108700 and WO 2005080382.
US patent application US 2008/0176860, discloses azabicyclo[3.1.0]hexyl-O-phenyl-oxazolidinone derivatives as antimicrobial agents. WO 05/005398 discloses phenyl oxazolidinone linked to azabicyclo[3.1.0]hexane moiety as antibiotics. PCT publications bearing number WO 03/027083, WO 04/089943, WO 04/033451, WO 05/005399 and WO 05/005422 disclose azabicyclo[3.1.0]hexyl-phenyl-oxazolidinone derivatives as antimicrobial agents. Other references include J. Med. Chem. 2005, 48, 5009 disclosing azabicyclo[3.1.0]hexyl-phenyl-oxazolidinones as antibacterials and J. Med. Chem. 2008, 51, 6558 disclosing biaryl oxazolidinones bearing azabicyclo[3.1.0]hex-6-yl ring system as antibacterials. Phenyl oxazolidinones linked to the cyclopropyl moiety of azabicyclohexane scaffold have been discussed in Biorg. Med. Chem. Lett. 2006, 16, 1126.
PCT patent application WO 05/082899, discloses phenyl oxazolidinones as antibacterial compounds. According to their Markush structure, the invention encompasses phenyl oxazolidinones linked to 3-azabicyclo[3.1.0]hexane core through nitrogen of azabicyclo hexane. However, Compound No. 32, (S)—N-{[3-(3-Fluoro-4-{3-(1α,5α,6α)-6-[N-methyl-N-(5-nitro-furan-2-yl)amino]-3-azabicyclo-[3.1.0] hexyl}phenyl)-2-oxo-oxazolidin-5-yl]methyl}acetamide, representing the Structure A has been wrongly interpreted by the databases (Thomson Pharma and Scifinder) as Structure B.
This Compound No. 32 neither falls under the coverage of the Markush of '899 patent application nor it is the actual invention. The synthetic procedure for its preparation and 1H NMR data given for it in '899 patent application also suggest Compound No. 32 to be Structure A.
The compounds of the present invention are structurally different from the known 3-azabicyclo[3.1.0]hexane derivatives.